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Episode #52

Failure and Fearlessness in Entrepreneurship

January 19, 2026 · 26:58

Total runtime: 26:58

Show notes

Failure and Fearlessness in the Entrepreneurship Journey | Power Up Your Life Podcast | Powered by GoBundance | Episode 52 with Anna David

Unlocking Success: Anna David's Journey as a Late Bloomer🏆📚

In this engaging episode of the Power Up Your Life podcast, hosts Mandy McAllister and Kelly Resendez chat with the dynamic and inspiring Anna David. Anna is a New York Times bestselling author, founder of Legacy Launchpad Publishing, and an accomplished media contributor. She shares her incredible journey as a late bloomer, making significant strides in her career at 46, and becoming a mom at 52. Anna discusses the importance of overcoming fear, finding mentorship, and the power of perseverance in entrepreneurship. Learn how she helps other entrepreneurs turn their stories into impactful books, and gain valuable insights into maintaining work-life balance as a mother and businesswoman. Tune in for an episode full of inspiration, practical advice, and empowering stories! 🚀✨

00:00 Introduction to Anna David
01:26 Anna's Journey and Achievements
02:21 Overcoming Obstacles in Business
07:37 Finding Mentors and Building Relationships
17:40 Balancing Motherhood and Entrepreneurship
20:51 Final Thoughts and Takeaways

💫 Find Anna on social media at Anna B. David
🌐 Websites mentioned in program:
https://annadavid.com/   
https://www.legacylaunchpadpub.com/   

✅ If this content resonated with you, drop a like, comment, and share with your friends! For the latest PUYL Podcast episodes and more, subscribe @GoBundanceWomen 

🚨 Find out more about our new upcoming platform, Power Up Your Life Now and more at https://GoBundanceWomen.com   

Chapters

Show transcript(35 blocks)
  1. Annie

    Man, guys, you are totally gonna agree with me that Anna David is this really dynamic firecracker in this next conversation. Anna David is a New York Times best selling author of eight books. She's also the founder of Legacy Launchpad Publishing, the leading hybrid publishing company for top entrepreneurs.

    A seasoned media contributor, she's appeared on Today, Good Morning America, The Talk, and Doctor. Drew, and she's delivered three, three TEDx Talks on building businesses and legacy. Her work has been featured in The New York Times, Time Magazine, Vanity Fair, and Cosmo, among others.

    Anna also hosts the Behind the Book Cover podcast and serves as book critic for KATU TV in ABC Portland, helping thought leaders turn stories into lasting impact. Here's Anna David. Hello, and welcome to the Power Up Your Life podcast powered by GoBundance Women. I'm Annie McAllister. And I'm Kelly Resendez. And today we have a real firecracker of a dynamo, my girl, Anna David. Hi, Anna. Hi, queen.

  2. Calling

    Remember that's what I'm calling you?

  3. Annie

    Yes. I do. I love it. I love everything about it. We had the opportunity to spend some time together, a while back in, Mexico. And since then, you've become a mama. So much has gone on in your life. You know, tell our audience before we get started just a little bit about who you are and your journey.

  4. Calling

    Okay. So I am the quintessential late bloomer. I didn't become an a student till my senior year in college. I figured out school at that point, how to do it well.

    Then I didn't, make money, real money, till I was 46. I did not figure it that part out. I mean, I made money, but, like, now, like, you know, barely. I so I didn't figure out how to do business till I was 46, and I didn't have a baby until I was 52, but he was born via surrogate. 53.

  5. Like

    First of all, holy moly. You look like you're, like, 30 years old. So whatever you're doing, girl, you just keep it up.

  6. Calling

    Not today, but thank you.

  7. Annie

    I love it. I I mean, we at GoBundance Women that you've spent a a ton of time with, we we focus on helping female entrepreneurs grow their influence and, you know, get unstuck when they feel stuck because community is that thing that most times takes people to that next level.

    So in your business, the the launchpad, the the publishing launchpad, I'm I'm very curious to know from all of the work that you do there, what do you see with your entrepreneurs and you personally? When you feel stuck, how how do you get them unstuck?

  8. Calling

    Well, it's a great question when it comes to books because there's all sorts of reasons why they get stuck. Oftentimes, ones I don't think they're conscious of, a lot of fear, false evidence appearing real that comes up as, avoidance. Our biggest problem as a business is that our clients start ghosting us. They pay us a fortune, and then they disappear. And it's insane, except fear is not sane.

    So, oftentimes, it's really good for me to just be direct. You know, Tamar, who you know, she was one who she was a good enough friend, and she had enough self awareness to go, oh, I'm scared. That's why I'm avoiding you. Most do not, and it's interesting.

    I was just last week at a mastermind where I a client who has been on our roster for two years, top paid top dollar the most you can pay and has not moved forward with his book. And I I saw him at at the lunch. I was like, I am doing an intervention on you. Come sit down. You are scared. And as of this morning, I put him with a new rider, and he emailed me. I'm so excited to move forward. Let's do this. So that's how we get them unstuck. We tell them.

  9. Like

    Yeah. Shake them down. Yeah. Yeah. So when when you think about getting stuck in your own business, I mean, you you just shared at the beginning that you didn't really get moving until you were about 46 years old. Yeah. Can you share a little bit more of what that that journey was like, how you found this career, and and what you guys actually do for people that are out there?

  10. Calling

    Yeah. And it's interesting. Stuck is not my thing. I it's like I've never experienced writer's block or whatever it is. I feel like that's an excuse. I I it's weird because it's not like I was stuck. I didn't know this whole world existed. I was absolutely moving forward. I was I never stopped. You know?

    And in the eyes of the world, I was very successful in that I had a New York Times best selling book. I was on the Today Show. I was doing all of these things, and I thought that was the only path. And it wasn't until I met my mentor who introduced me to this whole world of successful entrepreneurs that I understood there was another way.

    I never knew that there were people you could go to and say it's a $100,000, and they would go, oh, one payment or two. I was used to, can I can you pay me, $500 and them saying you're overcharging? So it was a whole new world that I couldn't believe existed.

  11. Annie

    Wow. A lot of it is, like, recognizing the worth of things too. Your own worth, your product's worth, your the things that you're doing. Because if it's worth that $100,000, it's a completely different sales process than ask an avatar. You know?

    I I think just the idea in general of being an entrepreneur and, you know, your path, having gone from writing fiction into helping other people have that thud factor of their own book Right. To to gain credibility. You know, what's something unconventional that you believe to be true in entrepreneurship that other people might not believe to be true? That was such a good question.

  12. Calling

    One thing in book publishing is all my I I I don't love the word competitors, but all the people I know who do what I do are very focused on book sales. You gotta sell a lot of books. I say I'd rather sell a 100 books to my ideal client than 10,000 to people who will whose lives won't change. So that's very specific to books.

    But I think in terms of entrepreneurship, this is not terribly original, but marketing is more important than ever. I would almost say I spend 75% of my time working on putting myself out there as, an expert in my field. And about, you know, the the eighty twenty, I probably spend 80% of my time on that because it it is a beast you have to feed all the time, but it pays off.

    It's not super quantifiable because most of it is when someone's already gonna work with you, they Google you, and they go, oh, she's got podcast, got this, she's got that. It you know, very few times is that I I listen to your podcast, and I'm hiring you because of that. So to me, that's as important, if not more than the work you actually do.

  13. Like

    Yeah. So great. You know, you mentioned before finding a mentor, and we've all heard the power of proximity. Like, tell us a little bit more. How did you find your mentor? How do you really ensure that your environment is supportive of of all your own goals?

  14. Calling

    Yeah. It's super interesting because I never heard of having a mentor, literally never heard of the concept until maybe twelve years ago, and my immediate response was like, where is my mentor? Why has my mentor not shown up for me? I would say I didn't ever experience a lot of them. It's not like I really had many professors in school that were like that or bosses. But I my first boss was amazing, but after that, I worked in magazines with completely abusive, horrible people. So that was opposite of what they were trying to do.

    But, of course, you know, the the teacher doesn't appear till the student is ready. So how much of that was me and my Yeah. Unwillingness to have the humility required? And Yeah. I think the misconception that a mentor is not just someone who goes and blindly helps you. A mentor is someone you help who then it I mean, in my experience, who then helps you. It's very mutual.

    I remember sort of learning about the concept of a mentor and looking at meetup groups in LA because I was like, I'm gonna find some badass, you know, CEO, female CEO to be my mentor. And and I couldn't really swing it, and then Joe Polish. Do you guys know Joe? Yeah. It just it was just this it's this beautiful story. It's like I saw him on Facebook, and I said, this man's talking about recovery from addiction, which is my topic, and he looks really cool. And I sent him he looks he looks successful in a way that I wanna be.

    I sent him a friend request. He ignore you know, he didn't even see it. He doesn't do that stuff. My sister-in-law, she was then my brother's girlfriend. I saw that she knew him. And I said, Maria, I wanna know this guy. You know, I saw they were Facebook friends. And she said, oh my god. I said, I sent him a friend request because he'll never see it. Let me just do a text intro. She did, and he's such an amazing guy. And, also, it's a testament to my sister-in-law that he had a lot of respect for her.

    And he just I think he just called me, and he's like, oh, I'm in LA. What are you doing? I'm shooting a or he looked me up. He again, speaking to that thing about the importance of building that up, he looked me up and he goes, wow. You know a lot about addiction. I'm doing a documentary on it. Do you wanna be in it? And he said, I'm in LA, and I I have a hotel room. Now when a man asks you to go to a hotel room, you should, of course, say no.

  15. Like

    Especially in LA.

  16. Calling

    Yes. Especially in LA. However, I just said yes, and I show up. I mean, it was like a Sunday day. Bad things can happen at any time, but still, it was not like, you know, Saturday night. And and we got and he has this whole crew set up in his hotel room. We do the interview, and then he says, I'm here for this conference called abundance three sixty. My friend Tony is speaking at it, and he gets a text, and it's from Tony Robbins. And I'm like, who is this guy?

    And then and so then I had just entered the world of Internet marketing because before I started my business, I kept, like, trying to sell courses and coaching and these things that were just not working for me. But before then, I was like, oh, I have this webinar, and I it's tomorrow, and I've prepped for it. I've studied this woman, Amy Porterfield, and I've done everything she suggests, and it's gonna be so awesome. Mhmm. But I'm I'm nervous. By the by the time I leave we have breakfast after the interview. By the time I get home, Amy Porterfield has left me a message saying, my friend Joe called me and said you're really nervous about your webinar. Do you want me to look at your slides? Like, this was crazy because I had studied her for a year. And, again, I'm like, who is this guy?

    So then he texts me, and he goes, do you wanna come to dinner with a bunch of people? So I I'm like, okay. And I go to dinner, and he seats me across from Dave Asprey, you know, who's this famous entrepreneur. And and something happened at that dinner. It's this long table. And at the end, a woman I didn't even speak to picked up the tab. And, like, of course, I'd been around, like, I'm in Hollywood, like, bougie fabulous people with tons of money, but I've never had the experience of someone I never even spoke to paying for my meal for no reason. And I said, this is a group I wanna be a part of.

    Sorry. This is such a long answer. But Joe said, do you wanna come to one of my genius network meetings? It's, you know, in a month. And I said, okay. But I wrote for the Huffington Post then. And so as I I said, I can write an article about it. And that, you know, I did that. It super helped him and thus began our relationship. We write books together. We do all sorts of things. That was seven years ago.

  17. Annie

    So I love that. It it is such a mutually beneficial thing that that you are showing up to serve someone that can also make introductions to you. Because it's all people. People are just people. You know, if they're incredibly successful, if they're, you know, the janitor, it doesn't people are just people.

    You know, I I think it's such a really, inspiring story that you said you didn't have anything figured out. You weren't making money until you were 46. Maybe there's entrepreneurs, listeners to this show that are, you know, late thirties, early forties, and and, you know, they want to figure out how to get to that next step. From your experience, tell me a couple actionable steps that helped you get that light bulb to go on, and maybe describe that light bulb a little bit.

  18. Calling

    Well, I didn't give up. I did not, and I think that was that was the reason. Like I said, I tried courses. I tried coaching, and I think it's really important to see what doesn't work and to be honest with yourself and to go, okay. I gave this everything. And, you know, I yeah. It's always kind of it can be hard to tell the difference between what is just not the universe's will and what is I need to work harder. Mhmm. And I a lot of people can confuse those things.

    So be really honest with yourself. If you have tried and you are getting blocked as you you know, the word blocked, everywhere you go and you are killing yourself and you're making no money at it, then then it is not your path, but your path is there. And I and I believe that the the longer it takes to find it, the more grateful you're going to be.

    So I would say don't listen to the experts who who say, oh, things like, if you create a course like I create a course, you're going to have the success that I have. I think it's really what I when with the book publishing, I don't say I can show you how to become a New York Times best selling author because I can't. I can't control that. What I can say is I can show you how to build an authority building book, and I can do that for you, and I can show you how to help that help you earn 7 figures from that because anybody I'm gonna work with has the ability to do that. But I I think avoid those people who say because I did this impossible thing, you became a millionaire from webinars. You can too because it's just not true.

  19. Like

    Love that. So great. So great. You know, I wanna dig into just something a little bit deeper. You know, you said you were kind of a part of the addiction, you know, space and whatnot.

    And, obviously, knowing you, like, your energy is contagious. Like, you're just that person that lights up a room. What have you really done for yourself from a personal growth perspective?

    You know, one thing that so many entrepreneurs don't realize is who we're being is as important as what we're doing. What are some of the things that you do to really ensure your energy is in alignment with your highest

  20. Calling

    power? Well, it almost never stops, not because I'm some saint, but because it's required for me to function. I I go to 12 step meetings. I work a 12 step program, which is super different than just going to meetings. I mean, it's sort of a day in, day out, you know, process of stepping away from your thinking to, see that you are not the thinker, if that makes sense.

    And the you know, it's like, I have an example from this morning, which is my boyfriend's family was visiting for the last four days, and this was coming off of me going to Genius Network, coming off of my mom visiting for just I'm spent, and it was really hard to have these lovely people in our home. And I couldn't sleep last night. You know, I told you guys that, and I was so angry at my boyfriend. We don't really fight, but I was just like, you know, how could he and blah blah blah and this and that. And then I read this newsletter I read every morning, which is by my friend Jeff Colbert. It's the spiritual newsletter that talked about about that, about you're not the thinker. And I meditated, and I was like, oh, I'm not mad at him. I'm not mad at him. Because, you know, that middle of the night spinning, you can really build a case about anybody.

    And so it's it's that. It's the meditating. I've been doing that twenty to forty minutes a day for twenty years. It's, praying. It's, I I do things like exercise and cold plunge, and, you know, I've sort of I consider all massage, I consider all of those things part of my spiritual practice pretty much.

  21. Annie

    It's so important. Yeah. Absolutely. I you know, another kind of deeper concept that I I wanna dig into, you know, being female entrepreneurs, the the experience of being a mom while being an entrepreneur and, you know, knowing many entrepreneurs get, tied into more hours, harder work can equal better results. Right?

    And when you are a mama at the same time as you're trying to scale a business, things change. You know? Talk to me a little bit about how, you know, being a mom and an entrepreneur at the same time have changed how you handle things.

  22. Calling

    Yeah. It's interesting because the year before he was born, I made two people on my team. I offered them partnership in my company because I thought, oh, I'm I'm just gonna stop working, and I I would need the business run. What's crazy is and they were wonderful. Neither of them are on my team anymore. It turns out there are better people for for this. They were great. And so I didn't know what my business was gonna really look like.

    I have a a partner who does so much. You know? He's the one who does the heavy lifting, so I'm lucky enough to be able to work when I as much as I want or not. And I've had guilt around it because guilt is just an essential part of parenting. And I've I've really had to work through it because it's okay that my boyfriend does more. It's okay. And it doesn't make me a bad mom.

    There are a lot of things I do that that he does. I mean, like, I don't think this kid would have a bath or be in school if it wasn't for me. You know? I do that stuff, but I find the things. But but so the balance is quite easy for me because of that.

    And I'm also someone I could write a book in in, like, Central Park Station. What's that called? You know, it's with Madison Square Garden, I can zoom in and focus if it's for five minutes, if it's so I I I'm very good at sort of jumping between things.

  23. Like

    Oh, that's so awesome. Well, I have adult children, And and I look back at that age, and I'm like, what the heck kinda energy were we running on? You know? Like, because you wake up in the morning, you don't get to decide what time you wake up. The the little wakes you up, and then you don't get to decide what time you go to bed, and it's just such a blur.

    But I'm here to tell you, like, it is it is all worth it, and, oh my gosh, they're the most amazing. You know? And I and I and I truly believe, And thank you for sharing that story because when you believe in infinite possibilities of what you can create, you can still have a successful business and be an amazing mom no matter what age you are, and and you really have have demonstrated that in your life that, you know, timing is everything. A lot of times, we try to control, and that's where it really where we have to let go.

    So I wanna ask you a little bit more about just the entrepreneurs that you work with. And so you you've kinda shared a little bit, you know, that many of them sabotage themselves by procrastinating or not doing other things. What would you to just speaking to all the entrepreneurs that are probably listening today, like, what do you believe is what is really needed in the world today for people to create more success in their business?

  24. Calling

    I think it is really truly like, it's sort of what I said before about learning to be honest with yourself because I don't know about other people, but I'm an amazing storyteller, and I tell myself the best stories of all. I'll believe you can believe anything because it's talking to you in your own voice, And it might be self sabotage, and it might be imposter syndrome, and it might be self hatred. But I think it's really important because being stuck is a mental thing. It's not real because, you know, it it came upon you, so it can leave.

    And so I think that I don't know. It's it's almost reminds me of people will say to me, oh my god. You're twenty five years sober. That must be so hard. And I always say, no. Before the before times were hard. This is easy, comparatively speaking.

    I find being successful and running a really big company a lot easier than not. And so I think that I think that people are scared of success, but what it gives you is freedom. It gives you the ability to say, I'm gonna work as much as I want and spend as much time with my kid as I want.

    And so and I think people shouldn't be afraid to delegate if possible if they're not in the financial situation yet, getting an intern, finding ways to not do the things that are gonna that are just gonna be busy work. I also find you know, I think one one of you said, you know, we sit at we sort of sit there and try to work harder. I feel like when I go and I get a massage, when I go into cold plunge, when I do things like that, I can actually free my brain up to make better decisions.

  25. Annie

    Totally. Space matters. Slack matters in your day. Yes. Yeah. It it's so incredibly important.

    There's been so many things that you've said, Anna, that have just hit me. And I I think my favorite though is the I didn't give up. That, you know, is this the will of the universe or is this, you know, that I just need to work a little bit longer, a little bit harder on on this thing to figure out if it is my path?

    Because that's where success comes is is when you, you know, lock and click into the right thing. Kelly, what what was your favorite takeaway?

  26. Like

    Oh my goodness. So many, and it's just been amazing having you here. But I loved the conversation about how when you were ready, the right person came into your life, and that one person ended up creating a domino effect for you both. And I believe wholeheartedly that when we get into that state, that is what we end up attracting. So I loved that part of it.

    And then, you know, just that that you get to create. Like, you got to create the business and the alignment in your personal life. The one thing that I would share with you is, like, the sooner you release the guilt, the better. I had the most amazing I don't know if you know Khloe Madonis, but she was with Tony Robbins initially and helped him with a lot of her stuff, and she mentored me a little bit. And in other countries, she's like, you people in America, like, what you put on yourself as a working mom, like, that is not the case in other countries, you know, in terms of expectations. So just let that stuff go.

    But thank you so much. And, Anna, one thing that we always love doing here at GoBundance Women and on the Power Up Your Life podcast is, like, what is one resource connection? How can we support you in in your business or your life?

  27. Calling

    Well, Kelly, years ago, we talked to you about doing a book. Remember?

  28. Like

    I'm working on my fourth one right now, so I've definitely read written written quite a few since then.

  29. Calling

    You have. We were gonna work with you on it. I was gonna say work with us on your books, but

  30. Like

    but Well, I think there could be some partnerships there, though, Anna. There's definitely opportunity.

  31. Calling

    I don't think I don't know if there's anything else. I think, you know, continue to serve this audience. Continue to, you know, give other women inspiration. And I would encourage them to join your, network if they're appropriate for it because it's the most fantastic group of women. Oh, thank you. Thank you for that. I beautiful.

  32. Annie

    But what is the best way for listeners to get ahold of you or, Legacy Launchpad?

  33. Calling

    Yeah. I'm on I'm on social media. I'm on Instagram and threads now and all of them at Anna b David. So and then legacy launch pad pub is the site, and anna david dot com is the site too.

  34. Annie

    That's awesome. We will make sure that that gets everything is in our show notes. And thank you everyone for joining us today on the Power Up Your Life podcast. If you know someone that has been trying really hard and hasn't made it click yet, they need this story in their life. Please send it to them.

    Like, subscribe, leave us a five star review. And if you need to power up your business, make sure you go to Power Up Your Life Now to look at all the resources that can help you do that. We will see you next week.

  35. Like

    Awesome. Thank you.